Medicinal Chemistry

Design, Synthesis, Antimicrobial and Anti-inflammatory Activity of N-Pyrazolyl Benzamide Derivatives

Abstract

Aneesa Fatima, Ravindra Kulkarni and Bhagavanraju Mantipragada

New N-Pyrazolylbenzamide derivatives which possess 2, 4-dinitrophenyl group were synthesized using 4, 4-dimethyl-3-oxo-pentanenitrile and 2, 4-dinitrophenyl hydrazine hydrochloride to afford an intermediate compound. The intermediate on auxiliary aroylation with substituted benzoyl chlorides in the presence of base yielded the subsequent N-Pyrazolylbenzamide derivatives (5a-l). The structures of newly synthesized compounds were elucidated by 1H NMR, FT IR and Mass spectral analysis. The anti-inflammatory activity of all newly synthesized was evaluated using carrageenan induced paw edema model and antimicrobial activity by serial dilution method. Six compounds (5d, 5f and 5h-k) showed consistently good anti-inflammatory activity in particular 4-trifluoromethyl-. N-[3'-t-butyl-1'-(2", 4"-dinitro)phenylpyrazol-5'-yl] benzamide (5h) was found to be the most effective among the other derivatives. The antimicrobial screening of all synthesized molecules showed that compounds 5f and 5h possess superior and encouraging activity against tested organisms